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Some mechanistic aspects regarding the Suzuki–Miyaura reaction between selected ortho-substituted phenylboronic acids and 3,4,5-tribromo-2,6-dimethylpyridine

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cris.lastimport.scopus2024-02-12T20:18:23Z
dc.abstract.enAtropisomers are very interesting stereoisomers having axial chirality resulting from restricted rotation around single bonds and are found in various classes of compounds. ortho-Substituted arylpyridines are an important group of them. A regio- and atropselective Suzuki–Miyaura cross-coupling reaction on 3,4,5-tribromo-2,6-dimethylpyridine was studied. Reactions with various amounts of ortho-substituted phenylboronic acids with 3,4,5-tribromo-2,6-dimethylpyridine gave a series of mono- di- and triarylpyridine derivatives which allowed to draw conclusions about the order of substitution. Also, the observed selectivity in the case of ortho-methoxyphenylboronic acid suggested an additional metal O-chelation effect in the transition state, apparently not present in the ortho-chloro analogues. The rotational barrier in selected atropisomers was determined on the basis of HT NMR and thermal epimerisation experiments. The structure of most presented atropisomeric derivatives of 2,6-dimethylpyridine was confirmed by single-crystal X-ray analysis. Racemic chiral, differently substituted atropisomers were also examined by 1H NMR spectroscopy in the presence of a chiral solvating agent. This regio- and atropselectivity may be generally applicable to other arylpyridine systems. A regio- and atropselective Suzuki–Miyaura cross-coupling process has been observed, giving an efficient access to a class of atropisomeric compounds. An opposite selectivity using a differently ortho-substituted phenylbornic acid was observed.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorBudzianowski, Armand
dc.contributor.authorPomarański, Piotr
dc.contributor.authorCzarnocki, Zbigniew
dc.contributor.authorMaurin, Jan
dc.contributor.authorRoszkowski, Piotr
dc.date.accessioned2024-01-26T07:53:04Z
dc.date.available2024-01-26T07:53:04Z
dc.date.copyright2018-09-11
dc.date.issued2018
dc.description.accesstimeAT_PUBLICATION
dc.description.financeNie dotyczy
dc.description.versionFINAL_PUBLISHED
dc.description.volume14
dc.identifier.doi10.3762/BJOC.14.214
dc.identifier.issn1860-5397
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/120205
dc.identifier.weblinkhttps://www.beilstein-journals.org/bjoc/articles/14/214
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofBeilstein Journal of Organic Chemistry
dc.relation.pages2384-2393
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.enarylpyridines
dc.subject.enatropisomerism
dc.subject.encross-coupling
dc.subject.enpalladium
dc.subject.enSuzuki–Miyaura reaction
dc.titleSome mechanistic aspects regarding the Suzuki–Miyaura reaction between selected ortho-substituted phenylboronic acids and 3,4,5-tribromo-2,6-dimethylpyridine
dc.typeJournalArticle
dspace.entity.typePublication